An Overview of my Long Term Projects

Currently I have a few big projects that I’m working on concurrently that all of my lab time is contributing to in one way or another. I thought it would be good to set down an outline of what these are.

Tetraphenylmethane total synthesis

My main interest is organic synthesis, and being fairly new to it, I still try to follow relatively well-trodden paths as I’m learning, so I look for interesting compounds that I can try to make that will challenge me and allow me to practice a wide variety of skills and try out reactions that are useful in many instances in organic syntheses. One of these that I have been plotting on for some time now is tetraphenylmethane. I chose it simply because it has an interesting structure, and everything needed to make it is accessible and relatively inexpensive. My total synthesis plan (which I drew up using ChemDraw) is shown here:

tetraphenylmethane-plan

So far, I have made bromobenzene, and today I made nitrobenzene, though I need to finish the workup tomorrow. I also made phosphorus tribromide, which will be used for brominating triphenylmethanol. I have all of the reagents that I need to complete this series of reactions, though I need to distill more diethyl ether from starting fluid to use as a solvent in a few of the reactions.

Martius yellow series

Another series of reactions that I’m starting to work on is the Martius yellow dye series described by Louis Fieser in his 1941 textbook of organic reactions. It is interesting as it produces many colorful compounds in series, all originally derived from 1-naphthol, which I happen to have an abundance of. I drew up an outline of the preparation of four of the dyes. There are seven in total, but the preparations of the ones not shown here require the use of acetic anhydride, which I do not have.

martius-yellow-series-1

My first attempt at the first of these reactions was unsuccessful, but I think I know what went wrong and will be able to make it work on the second try.

2-methyl-2-octanol and alkali metal preparation

Another project that has now been put on the back burner was researching tertiary alcohols that would be effective in catalyzing the reduction of sodium hydroxide to sodium metal. This has been a known problem in the amateur chemistry community for several years now, and it has begun to be addressed by Sciencemadness members now that the process has been studied fairly extensively on potassium. Since sodium alkoxides are more polar than their potassium analogues, they are not as soluble in the hydrocarbon solvent used for the reaction. Thus, in theory, sodium ions kill the catalyst and prevent the reduction from happening. Accordingly, longer chain alkoxides are less polar and would be more soluble. The alcohol that I decided to synthesize and test is 2-methyl-2-octanol, which I made using the Grignard reaction from 2-octanone and methylmagnesium iodide.

si-620

Before I even think about trying the reaction with sodium though, I need to make sure that I am competent at running it with potassium. Then I will need to try 2-methyl-2-octanol as the catalyst with potassium, and only if I can make that work will it be time to test it with sodium. It is certainly a lot of work for me to do on my own, and if there is a more invested inorganic chemist out there who is already proficient with potassium and would like to try it out, I would be more than happy to send them several mL of 2-methyl-2-octanol to experiment with.

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